The 12 Awards Of 2023: No.1 Unsexy Business, Wildest Predictions & More

About this video

Sam Parr, Shaan Puri, and guest Andrew Wilkinson review their ‘Millie Awards’ for the year, discussing standout companies, investments, content, and wild predictions. They dissect the craziest people they met (including a Soviet immigrant entrepreneur and a Turkish AI-driven agriculture founder), analyze their best and worst investments, and share their favorite books, shows, and business insights from the past year.

Key takeaways

• Sam highlights Val, a Soviet immigrant who built businesses generating $150-200M in annual revenue without raising capital, as an example of calm, logical execution despite unconventional work habits (working 3AM-4AM daily with five kids)
• Shaan’s best investment was Shepherd, a recruitment platform where they acquired a minority stake and drove 50% of new leads through their audience, tripling the already-large business in 6-9 months—demonstrating the power of combining a good existing business with trusted distribution
• Andrew’s biggest miss was not investing in Whatnot (now valued at ~$4B) despite early belief and introduction; he waited rather than pushing hard for a spot, illustrating that in angel investing, the misses on mega-winners matter more than scattered losses
• Tax-loss harvesting gone wrong: Shaan sold crypto at a loss for tax purposes but delayed buying back due to psychological barriers, missing a 35-40% rally and negating the tax benefit—a reminder that emotional decision-making undermines strategy
• In business acquisitions, deal structure (how you negotiate terms) matters more than in venture; Shaan structured a Shepherd investment where the company lent him money to buy his own stake, creating a win-win where both parties gained outsized value
• Andrew’s dream house project revealed that over-building to personal perfectionism and decision fatigue led to a 30% loss on sale; buying the second owner’s refined property is smarter than being the first perfectionist builder
• B2B influencer status is real: Sam and Shaan realized they function like Kim Kardashian for business audiences—promoting a good product with trusted distribution can drive massive adoption and value creation
• Managing a CEO requires restraint: Sam learned that jumping in to correct every mistake undermines delegation; only intervene on fatal errors and let CEOs learn from non-fatal mistakes to build ownership
• Unsexy businesses crush: Pantone makes $100M+ annually by repeatedly selling updated color books to designers and fashion houses; Hoffman Bros HVAC grew from $13M (2016) to ~$140M (2023) by systematizing and scaling

Episode details: published December 18, 2023 · 31K views · 1:09:35 long. Summary written by Self Growth Videos from the episode itself. The business ideas, figures and results discussed are the hosts’ and guests’ own claims, shared as brainstorming and entertainment — not verified facts and not investment advice.

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